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Merck
CN

SML0477

Sigma-Aldrich

棘霉素

≥98% (HPLC), HIF-1α inhibitor, powder

别名:

N-(2-Quinoxalinylcarbonyl)-O-[N-(2-quinoxalinylcarbonyl)-D-seryl-L-alanyl-3-mercapto-N,S-dimethylcysteinyl-N-methyl-L-valyl]-D-seryl-L-alanyl-N-methylcysteinyl-N-methyl L-valine (81)-lactone cyclic (37)-thioester, Quinomycin A

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关于此项目

经验公式（希尔记法）:
C51H64N12O12S2
化学文摘社编号:
512-64-1
分子量:
1101.26
UNSPSC代码:
12352200
NACRES:
NA.77

主要文件

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产品名称

棘霉素, ≥98% (HPLC)

质量水平

100

方案

≥98% (HPLC)

表单

powder

储存条件

desiccated

颜色

white to beige

运输

dry ice

储存温度

−20°C

SMILES字符串

S1C(C2N(C(=O)C(NC(=O)C(COC(=O)C(N(C(=O)C(N(C(=O)C(NC(=O)C(COC(=O)C(N(C2=O)C)C(C)C)NC(=O)c5nc6c(nc5)cccc6)C)C)C1)C)C(C)C)NC(=O)c3nc4c(nc3)cccc4)C)C)SC

InChI

1S/C51H64N12O12S2/c1-25(2)38-49(72)74-22-36(59-42(65)34-21-53-30-17-13-15-19-32(30)57-34)44(67)55-28(6)46(69)63(10)40-48(71)62(9)39(26(3)4)50(73)75-23-35(58-41(64)33-20-52-29-16-12-14-18-31(29)56-33)43(66)54-27(5)45(68)60(7)37(47(70)61(38)8)24-77-51(40)76-11/h12-21,25-28,35-40,51H,22-24H2,1-11H3,(H,54,66)(H,55,67)(H,58,64)(H,59,65)

InChI key

AUJXLBOHYWTPFV-UHFFFAOYSA-N

相关类别

应用

Echinomycin has been used for inhibition of hypoxia-inducible factor 1.

生化/生理作用

Echinomycin is an antitumor antibiotic and potent hypoxia inducible factor 1α (HIF-1α) inhibitor.
Echinomycin is an antitumor antibiotic and potent hypoxia inducible factor 1α (HIF-1α) inhibitor. It binds to DNA via bifunctional intercalation, blocking the binding of HIF-1α, a transcription factor important in tumor growth. Echinomycin selectively eliminated cancer stem cells in a study with mouse lymphoma and human AML xenogeneic models, eradicating the lymphomas. Recently, echinomycin was also found to act as an antibiotic adjuvant having synergistic effects with novobiocin in gram negative bacteria.

象形图

Skull and crossbonesHealth hazard
GHS06,GHS08

警示用语：

Danger

危险分类

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Repr. 2

储存分类代码

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000482804
0000482806
0000482806
0000482804
0000437257

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Antitumour drug-DNA interactions: NMR studies of echinomycin and chromomycin complexes.
X L Gao et al.
Quarterly reviews of biophysics, 22(2), 93-138 (1989-05-01)
Kenji Watanabe et al.
Journal of the American Chemical Society, 131(26), 9347-9353 (2009-06-12)
Natural products display impressive activities against a wide range of targets, including viruses, microbes, and tumors. However, their clinical use is hampered frequently by their scarcity and undesirable toxicity. Not only can engineering Escherichia coli for plasmid-based pharmacophore biosynthesis offer
S M Zimmermann et al.
Injury, 44(4), 570-575 (2013-02-13)
Heterotopic ossification (HO) frequently causes complications following orthopaedic and trauma surgery and may drastically reduce the postoperative outcome due to pain and joint contracture. Current therapeutic options include NSAID's and local radiation. However, both options of prevention show disadvantages such
Rationally engineered total biosynthesis of a synthetic analogue of a natural quinomycin depsipeptide in Escherichia coli.
Kenji Watanabe et al.
Chembiochem : a European journal of chemical biology, 10(12), 1965-1968 (2009-07-10)
Dilip V Jarikote et al.
Bioorganic & medicinal chemistry, 19(2), 826-835 (2011-01-05)
Echinomycin is a natural depsipeptide, which is a bisintercalator, inserting quinoxaline units preferentially adjacent to CG base pairs of DNA. Herein the design and synthesis of echinomycin mimetics based on grafting of two quinoxaline residues onto a macrocyclic scaffold (glycophane)
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